Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Comformational and Complexational Properties of Distal Dialkyl Ester Derivatives of p-tert-Butylcaliz[4]arene

  • Published : 1997.01.20
Download PDF
⟨ Previous Next ⟩

Abstract

Complexation of primary alkylammonium ions by 1, 3-distal calix[4]arene diesters was studied by NMR spectroscopy. The guest alkylammonium ions are found to bind mainly to the two ester moieties and are oriented outward with respect to the cone cavity of the host, forming exo-type complexes unlike the case of alkylammonium-calix[6]arene systems. Measurement of T1 also revealed that the primary binding site is the two ester moities and phenolic OH groups. The temperature dependence of the chemical shifts of phenolic OH protons in these diesters correlates with the basicity of the solvent moderately well and the temperature coefficients of their chemical shifts are found to significantly decrease upon complexation with propylammonium ion.

Keywords

References

  1. Angew. Chem. Int. Ed. Engl. v.34 Bohmer, V.
  2. Calixarenes; A Versatile Class of Macrocyclic Compounds Vicens, J.(ed.);Bohmer, V.(ed.)
  3. Calixarenes Gutsche, C. D.
  4. J. Org. Chem. v.57 Iwamoto, K.;Shinkai, S.
  5. J. Am.Chem. Soc. v.116 Ikeda, A.;Shinkai, S.
  6. Chem. Lett. Araki, K.;Shinkai, S.;Matsuda, T.
  7. Angew. Chem. Int. Ed. Engl. v.33 Ungaro, R.;Casnati, A.;Ugozzoli, F.;Pochini, A.;Dozol, J.-F.;Hill, C.;Rouquette, H.
  8. J. Am. Chem. Soc. v.113 Groenen, L. C.;van Loon, J.-D.;Verboom, W.;Harkema, S.;Casnati, A.;Ungaro, R.;Pochini, A.;Ugozzoli, F.;Reinhoudt, D. N.
  9. J. Am. Chem. Soc. v.117 Casnati, A.;Pochini, A.;Ungaro, R.;Ugozzoli, F.;Arnaud, F.;Fenni, S.;Schwing, M.-J.;Egberink, R. J. M.;de Jong, F.;Reinhoudt, D. N.
  10. J. Chem. Soc., Perkin Trans. 2 Harrowfield, J. M.;Richmond, W. R.;Sobolev, A. N.;White, A. H.
  11. J. Chem. Soc., Chem. Commun. Beer, P. D.;Chen, Z.;Drew, M. G. B.;Gale, P. A.
  12. J. Chem. Soc., Perkin Trans. 1 Collins, E. M.;McKervey, M. A.;Madigar, E.;Moran, M. B.;Owens, M.;Ferguson, G.;Harris, S. J.
  13. J. Chem. Soc., Perkin Trans. 1 Fujimoto, K.;Nishiyama, N.;Tsuzuki, H.;Shinkai, S.
  14. The Aldrich Library of $^{13}C$ and ¹H FT NMR Spectra Pouchert, C. J.;Behnke, J.
  15. J. Am. Chem. Soc. v.103 Gutsche, C. D.;Dhawan, B.;No, K. H.;Muthukrishnan, R.
  16. Chem. Lett. Ahn, S.;Chang, S.-K.;Kim, T.;Lee, J. W.
  17. The Hydrogen Bond Vinogradov, S. N.;Linnell, R. H.
  18. Tetrahedron v.47 Groenen, L. C.;Ruel, B. H. M.;Casnati, A.;Verboom, W.;Pochini, A.;Ungaro, R.;Reinhoudt, D. N.
  19. J. Am. Chem. Soc. v.109 Reinhoudt, D. N.;Dijkstra, P. J.;in't Veld, P. J. A.;Bugge, K. E.;Harkema, S.;Ungaro, R.;Ghidini, E.